Santo D'Ascanio began competing at age 12 for Harold Paulson and the Portland Boys Club during its inaugural season of 1932.

He was a four-time Maine AAU diving champion.  During his diving career, he compiled a record of 160 wins against five losses; three coming before he was 14 years old.

He won the Maine High School Diving title in 1933 as a freshman at Deering High School. 

He transferred to Portland High School as a sophomore and went on to win three more state titles, setting state diving score records each year. 

He won two New England diving titles and two All American rankings in 1935 and 1936.  He was Honorable Mention All American in 1934.

He went on to help coach diving for the Portland Boys Club and Portland High School until graduating from Officer Candidate School and becoming a 2nd Lieutenant in the U.S. Army serving in Europe during WWII.